Computational characterisation of the charge-transfer and T-shaped molecular complexes of N-methyl imidazoline-2-thione and N-methyl imidazolidine-2-thione with the dihalogens Br2 and I2

Molecular Simulation

Volumn 36, Issue 3, 2010, Pages 212-220

  Kosmas, Agnie Mylona ^a   Papayannis, Demetrios K ^a  

^a UNIVERSITY OF IOANNINA   (Greece)

Author keywords

Charge transfer; Halogen bonding; Hypervalent complexes

Indexed keywords

BASIS SET SUPERPOSITION ERRORS; CHARACTERISATION; ELECTRON DONORS; ELECTRON-ACCEPTOR; HALOGEN BONDING; IMIDAZOLINES; INTERESTING INFORMATION; METHIMAZOLE; MOLECULAR COMPLEXES; MOLECULAR CONNECTIVITY; NATURAL BOND ORBITAL ANALYSIS; ORGANIC SPECIES; PERTURBATION ENERGY; QUANTUM MECHANICAL; RELATIVE STABILITIES; SECOND ORDERS; STABILISATION; STRUCTURAL CHANGE;

BROMINE; CHARGE TRANSFER; COMPLEXATION; ELECTRONIC STRUCTURE; ION EXCHANGE; MASS TRANSFER; MOLECULAR ORBITALS; QUANTUM THEORY; SPECTROSCOPIC ANALYSIS; SULFUR; SYSTEM STABILITY;

HALOGEN COMPOUNDS;

EID: 77649132393     PISSN: 08927022     EISSN: 10290435     Source Type: Journal    
DOI: 10.1080/08927020903186592     Document Type: Article

References (29)

1. A. Karpfen, Theoretical characterization of the trends in halogen bonding, in Halogen Bonding Fundamentals and Applications, Vol. 126, P. Metrangolo and G. Resnati, eds., Structure and Bonding, Springer, Berlin, 2008, pp. 1-15.
2. A.C. Legon, The interaction of dihalogens and hydrogen halides with Lewis Bases in the gas phase: An experimental comparison of the halogen bond and the hydrogen bond, in Halogen Bonding Fundamentals and Applications, Vol. 126, P. Metrangolo and G. Resnati, eds., Structure and Bonding, Springer, Berlin, 2008, pp. 17-64.
3. W.T. Pennington, T.W. Hanks, and H.D. Arman, Halogen bonding with dihalogens and interhalogens, in Halogen Bonding Fundamentals and Applications, Vol. 126, P. Metrangolo and G. Resnati, eds., Structure and Bonding, Springer, Berlin, 2008, pp. 65-104.
4. K.E. Riley and P. Hobza, Investigations into the nature of halogen bonding including symmetry adapted perturbation theory analyses, J. Chem. Theory Comput. 4 (2008), pp. 232-242.
5. A. Gavezzotti, Non-conventional bonding between organic molecules. The 'halogen bond' in crystalline systems, Mol. Phys. 106 (2008), pp. 1473-1485.
6. W. Wang and P. Hobza, Origin of the X - Hal (hal = Cl, Br) bond-length change in the halogen-bonded complexes, J. Phys. Chem. A 112 (2008), pp. 4114-4119.
7. K.E. Riley, J.S. Murray, P. Politzer, M.C. Concha, and P. Hobza, Br···O complexes as probes of factors affecting halogen bonding: Interactions of bromobenzenes and bromopyrimidines with acetone, J. Chem. Theory Comput. 5 (2009), pp. 155-163.
8. C. Laurence, M.J. El Ghomari, J-Y. Le Questel, M. Berthelot, and R. Mokhlisse, Structure and molecular interactions of anti-thyroid drugs. Part 3. Methimazole: A diiodine sponge, J. Chem. Soc. Perkin Trans. 2 (1998), pp. 1545-1551.
9. A.C. Legon, Angular and radial geometries, charge transfer and binding strength in isolated complexes B···ICl: Some generalizations, Chem. Phys. Lett. 314 (1999), pp. 472-480.
10. 2 molecular complexes, J. Am. Chem. Soc. 122 (2000), pp. 2300-2308.
11. V. Daga, S.K. Hadjikakou, N. Hadjiliadis, M. Kubicki, J.H.Z. dosSantos, and I.S. Butler, Synthesis, spectroscopic and structural characterization of novel diiodine adducts with the heterocyclic thioamides, thiazolidine-2-thione (tzdtH), benzothia-zole-2-thione (bztzdtH) and benzimidazole-2-thione (bzimtH), Eur. J. Inorg. Chem. (2002), pp. 1718-1728.
12. C. Ouvrard, J.-Y. Le Questel, M. Berthelot, and C. Laurence, Halogen-bond geometry: A crystallographic data-base investigation of dihalogen complexes, Acta Cryst. B 59 (2003), pp. 512-526.
13. 2 complexes, J. Mol. Struct. (THEOCHEM) 710 (2004), pp. 77-84.
14. 2] in a one-step reaction, Eur. J. Inorg. Chem. (2004), pp. 960-963.
15. G.J. Corban, S.K. Hadjikakou, N. Hadjiliadis, M. Kubicki, E.R.T. Tiekink, I.S. Butler, E. Drougas, and A.M. Kosmas, Synthesis, structural characterization and computational studies of novel diiodine adducts with the heterocyclic thioamides N-methybenzothiazole-2-thione and benzimidazole-2- thione: Implications with the mechanism of action of antithyroid drugs, Inorg. Chem. 44 (2005), pp. 8617-8627.
16. M.C. Aragoni, M. Arca, F. Demartin, F.A. Devillanova, A. Garau, F. Isaia, V. Lippolis, and G. Verani, DFT calculations, structural and spectroscopic studies on the products formed between IBr and N,N′- dimethylbenxoimidazole-2(3H)-thione and -2(3H)-selone, J. Chem. Soc. Dalton Trans. (2005), pp. 2252-2258.
17. M.C. Aragoni, M. Arca, F.A. Devillanova, P. Grimaldi, F. Isaia, F. Lelj, and V. Lippolis, Kinetic and thermodynamic aspects of the CT and T-shaped adduct formation between 1,3-dimethylimidazo-line-2-thione (or-2-selone) and halogens, Eur. J. Inorg. Chem. (2006), pp. 2166-2174.
18. 2, IBr and ICl, J. Mol. Struc. (THEOCHEM) 851 (2008), pp. 175-182.
19. 2. Implications for the mechanism of action of methimazole-based antithyroid drugs, J. Med. Chem. 51 (2008), pp. 4050-4053.
20. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, V.G. Zakrzewski, J.A. Montgomery, Jr., R.E. Stratmann, J.C. Burant, S. Dapprich, J.M. Millam, A.D. Daniels, K.N. Kudin, M.C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G.A. Petersson, P.Y. Ayala, Q. Cui, K. Morokuma, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J. Cioslowski, J.V. Ortiz, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P.M.W. Gill, B.G. Johnson, W. Chen, M.W. Wong, J.L. Andres, C.M. Head-Gordon, E.S. Replogle, and J.A. Pople, Gaussian 98 (Revision A.7), Gaussian Inc, Pittburgh, PA, 1998.
21. W.R. Wadt and P.J. Hay, Ab initio effective core potentials for molecular calculations. Potentials for main group elements Na to Bi, J. Chem. Phys. 82 (1985), pp. 282-298.
22. 2, J. Phys. Chem. A 101 (1997), pp. 4409-4415.
23. 2 molecules, and implications on the performance of dye-sensitized solar cell, J. Photochem. Photobiol. A: Chem. 181 (2006), pp. 268-273.
24. 3) polyoxides, Mol. Phys. 102 (2004), pp. 299-306.
25. A.K. Wilson, D.E. Woon, K.A. Peyerson, and T.H. Dunning, Gaussian-basis sets for use in correlated molecular calculations. IX. The atoms gallium through krypton, J. Chem. Phys. 90 (1989), pp. 1007-1023.
26. A. Bergner, M. Dolg, W. Küchle, and H. Stoll, Ab initio energy-adjusted pseudopotentials for elements of groups 13-17, Mol. Phys. 80 (1993), pp. 1431-1441.
27. J.P. Bowen, J.B. Sorensen, and K.N. Kirschner, Calculating interaction energies using first principle thearies: Considerationon of basis set superposition error and fragment relaxation, J. Chem. Educ. 84 (2007), pp. 1225-1229.
28. B.P. Prascher and A.K. Wilson, A computational study of dihalogen-μ-dichalcogenides: XAAX (X = F, Cl, Br; A = S, Se), J. Mol. Struc. THEOCHEM 814 (2007), pp. 1-10.
29. 13C NMR studies on CT complexes between some thiohydantoins and molecular diiodine, Heter. Chem. 5 (1994), pp. 65-71.